Cefdinir

HCID 6915944CAS 91832-40-5

Grundinformationen

Standard-SMILES
C=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\O)c3csc(N)n3)[C@H]2SC1
InChIKey
RTXOFQZKPXMALH-GHXIOONMSA-N
Summenformel
C14H13N5O5S2
Durchschnittliche Molmasse
395,4 g/mol
Monoisotopische Masse
395,03581052

Überblick

Cefdinir is a cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino- and 3-vinyl side groups. It has a role as an antibacterial drug. It is a cephalosporin and a ketoxime.

Namen und Bezeichner

Bevorzugter Name
Cefdinir
IUPAC
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Englischer Name
Cefdinir
Summenformel
C14H13N5O5S2
Molmasse
395.41

Namen und Synonyme

cefdinir91832-40-5OmnicefCefzonCFDNCefdinirumFK 482FK-482CI-983Cefdinir anhydrousDTXSID8046084BMY-28488
Weitere Namen anzeigen
syn-7-[2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid7-[2-(2-AMINOTHIAZOL-4-YL)-2-HYDROXYIMINOACETYLAMINO]-8-OXO-3-VINYL-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2(6R,7R)-3-Vinyl-7-[(2-amino-4-thiazolyl)[(Z)-hydroxyimino]acetylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid8-[2-(2-amino-1,3-thiazol-4-yl)-1-hydroxy-2-nitroso-ethenyl]amino-4-ethenyl-7-oxo-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylicacid(6R,7R)-7α-[[(2-Amino-4-thiazolyl)[(Z)-hydroxyimino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo--5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid[6R-[6α,7β(Z)]]_7-[[(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyimino-acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CI0FAO63WCPD-134393NSC-758926CHEBI:3485CI983FK482DTXCID20820060(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Datenbank-Bezeichner

CAS
91832-40-5
PubChem CID
6915944
DTXSID
DTXSID8046084
ChEMBL
CHEMBL927
ChEBI
CHEBI:3485
UNII
CI0FAO63WC
EC Number
643-088-1
Nikkaji
J227.563E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0
Polarare Oberfläche (TPSA)
212 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
10
Frei drehbare Bindungen
5
Schwere Atome
26

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

LogP-0.2
Solubility8.78e-02 g/L
Human Drugs · 3 Einträge

Breast Feeding; Lactation; Anti-Infective Agents; Antibacterial Agents; Cephalosporins;

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point>135
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
180 °C · >180°C dec.
Dichte
1.89 · 1.89±0.1 g/cm3(Predicted)
storage temp.
2 · Keep in dark place,Sealed in dry,2-8°C
Löslichkeit
dilute HCl: slightly soluble
pka
9.7 · 9.70(at 25℃)
Aggregatzustand
solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]

P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (20%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Cefdinir

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
3
hs_code
2941906000
RTECS-Nr.
XI0367250
Toxizität
LD50 orl-rat: >5600 mg/kg IYKEDH 23,93,1992
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingThe plasma protein binding of cefdinir ranges from 60% to approximately 70%.
Pharmacodynamics · 1 Eintrag

Cefdinir is a bactericidal agent that treats bacterial infections by interfering with cell wall synthesis. Cefdinir exerts broad-spectrum activity against a variety of gram-positive and gram-negative bacterial infections. It is effective against several beta-lactamase enzyme producing bacteria. As a result, many organisms that are resistant to other cephalosporins may be susceptible to cefdinir.

Mechanism of Action · 1 Eintrag

Five-member thiazolidine rings that make up penicillins are replaced in cephalosporins by a six-member dihydrothiazine ring, conferring greater bactericidal activity. This 6-member ring enables cefdinir and other cephalosporins to resist inactivation by certain bacterial enzymes. With a mechanism similar to other beta-lactam antibiotics, the bactericidal activity of cefdinir is caused by the inhibition of cell wall synthesis via binding to penicillin-binding proteins (PBPs). Cefdinir, like other cephalosporins, penetrates the bacterial cell wall, combats inactivation by beta-lactamase enzymes, and inactivates penicillin-binding proteins. This interferes with the final step of transpeptidation in cell walls, eventually leading to cell lysis, which eventually leads to the death of bacteria that are susceptible to this drug. Cefdinir has shown affinity to penicillin protein binding proteins 2 and 3. It has also been shown to inhibit transpeptidase enzymes of various bacteria, which may play a role in its bactericidal action. One in vitro study suggests that cefdinir inhibits myeloperoxidase release extracellularly. The impact of this potential drug target in relation to its mechanism of action is unknown.

Biological Half-LifeThe average plasma elimination half-life is about 1.7 hours in adults. In children and healthy infants, plasma elimination half-life ranges from 1.2–1.5 hours.
Metabolism/MetabolitesThis drug is not significantly metabolized and its pharmacological actions are mainly attributed to the parent drug.

Verwendung und Herstellung

UsesUse (kg) in USA (2002): 11300
Anwendungen · 2 Einträge

BeschreibungCefdinir is an orally active, beta-lactamase stable cephalosporin with a broad spectrum of activity. Compared to other oral cephalosporins, cefdinir is more potent against Gram-positive bacteria, especially Staphylococci. Its activity against Gram-negative bacteria such as E.coli,K. pneumoniae and P.mirabilis is similar to cefixime, but superior to cefaclor and cephalexin.

VerwendenA Cephalosporin antibiotic structurally similar to Cefixime

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino- and 3-vinyl side groups.

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